


First Time Wincest

by ForTheLoveOfChuck



Category: Supernatural
Genre: First Time, First Time Wincest, M/M, Wincest - Freeform
Language: English
Status: Completed
Published: 2016-08-09
Updated: 2016-08-09
Packaged: 2018-08-07 15:54:08
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,553
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7720771
Author URL: https://archiveofourown.org/users/ForTheLoveOfChuck/pseuds/ForTheLoveOfChuck





	First Time Wincest

The daylight wanes softly through the motel window, making Dean stir and realize he’s not alone in his bed. He carefully untangles his sleeping brother from him and goes to the bathroom. 

He returns to a still sleepy Sam sitting up in the middle of his bed. “Hey Sam, wanna talk about it?” He asks, knowing damn good and well that they won’t. He smiles when Sam reaches up to rub the gunk from his eyes. 

“Nah. I’m good.” He shrugs, pulling the covers from his lap and going into the bathroom. When he returns his face is pink, “Uhh…. Dean…”

His brother looks up, confused. “What’s up?” 

“I think you need to learn how to clean up after yourself.” He holds a sticky, damp hand and points to the side of his boxers. “Did you pee yourself or something?”

“No. I didn’t piss myself.” He answers, appalled at the thought. “It’s uh. Something else. Maybe you shouldn’t just randomly climb into my bed then.” He tries to defend himself instead of getting embarrassed. 

“You’re right. I shouldn’t have gotten into a bed with your come puddle.” He snarks, wiping his hand off on his other hip and stripping the shorts by his bed before clawing through his duffel to find clean ones. 

“Sam…” Dean says, strained. 

“Dean. It’s okay. We all do it. I typically wait until I’m alone to jack off though, goes better that way. No distractions.” He doesn’t even look up at his brother as he grabs the boxers and a pair of sweats. He pulls his shirt off and stands there nude as he finally catches Dean’s gaze. Which is right on his exposed crotch. “Something you want to tell me Dean?”

Dean breaks his gaze at his brother’s junk, his face turning bright red as he tries to play it off like he didn’t do it. “Nah. Nope. Nothing at all Sammy. You?”

Sam laughs, his dark voice easing some of Dean’s embarrassment. “Yeah Dean. I do.” He searches his brother’s face for any sign of fear. “I’ve got feelings for you.” 

Sam was always the emotional one, the one to jump off a cliff and damn the consequences, but Dean never expected Sam to say something like that. And it makes his heart jump a little. “You what?” Is all he can stutter out, his surprise obvious in his expression. 

“I like you Dean. A lot.” He shrugs, knowing it would be hard for his brother to accept. “And it’s okay if you don’t feel the same way.” 

He hadn’t ever let himself think about it, but he’d always felt close to his brother. Too close. He didn’t think Sam felt the same way, so he just didn’t let himself feel it. Making sure his wet dreams stayed secret, and sticking to all the blondes so he didn’t have to think about the brunette at home. Even when home was a shitty motel room in southern Kansas. He looks at his fingers, trying to calm his thoughts that were making his crotch hard to ignore. 

“Dean? Are you okay?” Sam asks, watching Dean’s face carefully where he’d been discussing with himself silently for a few minutes. 

He looks up, startled a bit. “Yeah. Of course I’m okay Sammy. Why wouldn’t I be?” He tries to smile and tell his brother that nothing’s changed. 

“Dean. We can just ignore this happened if you want to. I won’t bring it up again.” He tries to reason, letting Dean take the lead. Sam knows his brother well enough to know he needs the control of a situation. 

“I can’t really do that.” He sighs, looking up at his brother as he sits lower in his chair to take pressure from the erection stiffening between his thighs. He just can’t decide if it’s what they should do. 

“I could fix that.” Sam suggests, taking a step closer to his brother. “If you’re okay with it of course.” He smiles, meeting his older brother’s emerald eyes as he extends his hand to him. 

Dean swallows, closing his eyes and opening them again seconds later with resolve. He nods, taking his brother’s outstretched hand and standing up. He starts to roll the waistband on his boxers down his hips, but Sam’s hands cover his to stop him. 

“Wait. I want our first time to be done right.” Sam smiles, taking Dean’s fingers away from the band of his shorts and covering his hips again with his own hands. He leans in and softly captures Dean’s mouth with his, kissing his brother slowly. His hands pull Dean to him as he deepens the kiss, running his tongue along his brother’s bottom lip before exploring the rest of his mouth too. He leaves a short trail of kisses along his brother’s jaw before grabbing the hem and pulling Dean’s t-shirt over his head. 

“Are you sure you’re okay with this?” Dean asks, watching half-curious half-distracted as his brother kisses down his chest. 

Sam nods, continuing to kiss down Dean’s belly and pausing when he reaches the waistband of his boxers. He smiles, sliding the underwear down his brother’s hips and helping him to step out of them. He runs his hands down Dean’s hips, cupping his ass as he leaves kisses around the entire length of his brother’s erection. Meeting Dean’s gaze, he takes his big brother’s cock into his mouth.

“Always knew you had a big mouth Sammy.” Dean groans, watching his brother intently as he sucks on his cock. His little brother’s head bobbing brings him closer and closer with every time he carefully slides his teeth along the bottom of Dean’s erection. 

Sam learned how to be with men in college, not being afraid to experiment. He chuckles, coming off of Dean with a ‘pop’ when he knows his brother is close to coming. He kisses his way back up before claiming Dean’s mouth again. 

“Sam. Don’t wanna ruin the fun or anything, but I don’t really have any experience with men.” He stutters out, embarrassed. 

Sam kisses him quickly once more, laughing quietly. “Well, luckily for you, I do have experience. Go sit on the bed, I’ll show you.” He gestures for the bed, waiting until his brother sits down to grab the small bottle of lube from his bag. He hands the bottle to Dean to hold after he squirts a fair amount on his fingers. He then bends at his waist so his ass is near Dean and starts opening himself up by fingering himself around his rim and using his slick fingers to relax the muscles. He stands up for a few seconds, holding out his hand and putting some of the lubricant on his brother’s fingers before bending back down. 

Closer to his brother this time, Sam encourages Dean to try it. “Dean, I like this, just put your fingers in and move them around. It’s not as weird as you think.” He takes a deep breath, relaxing around his brother’s fingers. After a few seconds he starts to push himself back on them, grinding down on the feeling of his brother fingering him and getting him ready. 

“Sam,” Dean whispers, “are you ready?” He wipes his fingers on the sheet under him when Sam stands back up. 

“I’m always ready for you Dean.” He smiles, moving Dean so he’s lying on his back up the mattress. He climbs on top of the bed, kneeling over Dean’s stomach. “Are you ready De’?” He asks, knowing Dean’s hesitation. 

When Dean nods firmly, Sam moves so he’s right over his brother’s cock and takes him in a little at a time until their hips meet. He takes a few breaths, getting used to the feeling of his brother’s cock in him, before experimentally lifting himself up a few inches and coming back down. 

“De’ open your eyes, please.” Sam whispers, searching his brother’s face for any sense of regret or remorse. 

“I’m right here Sammy. We’re here together man.” He chuckles, sitting up enough to kiss Sam. He lifts Sam at the hips and sets a slow pace, moving their bodies together. Sam’s the one to pick the pace up, finding the spot he spent so long with an old boyfriend getting used to. Every time Dean thrusts up into Sam he hits that spot and it punches another little moan out of his brother. 

“Sammy. I know you’re close to coming, Come for me baby.” He whispers, wrapping a hand aroung his brother’s cock and stroking it in time. Just a few strokes later, Sam spills between them and paints his brother’s chest with come. The Sam’s orgasm pushes Dean over the edge and he comes deep in his brother. 

After, Sam slips off Dean and lies down beside him. He pulls the duvet over them both and hugs Dean close to him. “Hey Dean?”

Dean lies with his eyes closed, mumbling back. “Yeah Sammy?”  
Sam bites his bottom lip, running through the scenario again in his head. “Was that okay. Were you okay with what just happened?”

Dean pulls him closer, kissing his younger brother’s forehead sleepily. “Yeah Sam. Wouldn’t have done it if I wasn’t okay with it. Now go to sleep.”

Sam nods, accepting Dean’s response and dozing off next to his big brother.


End file.
